Biphasic product comprising hyaluronic acid and / or salts thereof

Sophorolipids facilitate rapid separation of clear and transparent phases in two-phase cosmetic products with hyaluronic acid, addressing cloudiness issues and eliminating the need for benzethonium chloride.

WO2026046577A1PCT designated stage Publication Date: 2026-03-05BEIERSDORF AG
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Patent Information

Application Number
PCT/EP2025/070046
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-09-02
Filing Date
2025-07-14
Publication Date
2026-03-05

AI Technical Summary

Technical Problem

Existing two-phase cosmetic products containing hyaluronic acid and/or its salts suffer from prolonged cloudiness and difficulty in achieving transparent phases due to high interfacial tension and density differences, necessitating the use of benzethonium chloride, which is increasingly undesirable.

Method used

Incorporating sophorolipids into the formulation with hyaluronic acid and/or its salts results in rapid separation of clear and transparent aqueous and oil phases without benzethonium chloride, using specific ratios and components.

Benefits of technology

The addition of sophorolipids enables transparent phases to form quickly after mixing and remain separate, enhancing product clarity and avoiding the need for benzethonium chloride.

✦ Generated by Eureka AI based on patent content.

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Abstract

A biphasic product containing hyaluronic acid.
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Description

[0001] Two-phase product containing hyaluronic acid and / or its salts

[0002] The present invention relates to a cosmetic two-phase product comprising organic acid components and hyaluronic acid and / or their salts.

[0003] Cosmetic products generally serve not only to make one look beautiful and attractive, but also contribute significantly to increased self-esteem and well-being. Consumers often apply decorative cosmetics to improve their appearance. However, these products are removed from the skin in the evening before going to bed. Cosmetic cleansing products are used for this removal; these products offer particularly effective cleansing without causing skin irritation.

[0004] A typical category of these cleaning products are cosmetic two-phase products, which are mixed by shaking before use. After use, the products separate within a short time. The presence of two separate phases is indicated to the consumer, for example, by the different colors of the phases. They consist of a specific proportion of an oil phase and a water phase.

[0005] In the area of ​​cleansing products, it has been shown that two-phase systems offer better cleaning performance, especially with waterproof makeup. Here, the effective cleansing action of oils is combined with water, which minimizes the oily residue.

[0006] To form a two-phase product, a phase containing water and a phase containing oil are required. At rest, these two phases are clearly distinguishable. Due to their different densities, these two phases do not mix spontaneously and thus form a horizontally separated two-phase system. By introducing energy, for example by shaking, the phases can be briefly mixed. However, due to the density difference and the high interfacial tension (IFS) of oil compared to water, a very rapid separation back into the two phases occurs.

[0007] In addition to their cleansing effect, it is also desirable that these products offer further benefits for the skin. One possibility is to add certain hydroxy acids to the formulations.

[0008] Hydroxy acids (or simply hydroxy acids) are naturally occurring carboxylic acids. The following hydroxy acids are of particular importance for human skin. One component is hyaluronic acid and / or its corresponding salts. Hyaluronic acid is a gel-like substance that occurs naturally in the body. It is found primarily in the skin, joints, eyes, and connective tissue. Hyaluronic acid can absorb more than 1,000 times its weight in water, thus helping to maintain the skin's moisture content. Thanks to these properties, hyaluronic acid is an excellent active ingredient in anti-aging creams and serums that keep the skin soft and supple.

[0009] If a specialist attempts to incorporate the components existing above into a product that has two separately separated phases in its resting position, this can lead to significant product disadvantages.

[0010] One disadvantage of products containing such acid components is that the aqueous and / or oil phase of the two-phase system remains cloudy for an extended period after mixing. This means that a clearly separated phase is not present. Furthermore, it is often impossible to produce transparent aqueous and / or oil phases in the first place.

[0011] The object of the present invention was to eliminate this disadvantage and to provide two-phase systems that, in their resting state, form clear and transparent aqueous phases separately from an oil phase particularly quickly, wherein the formulations are to contain the aforementioned acid component. Furthermore, the oil phases should also exhibit a transparent appearance in their resting state.

[0012] Previously, benzethonium chloride was often used in such formulations to enable rapid phase clarification. However, this ingredient is increasingly criticized, leading consumers to desire formulations without benzethonium chloride. Consequently, there was a need to provide alternative products with the same technical effect.

[0013] EP 2732805 A1 discloses two-phase preparations which contain alkyl glucosides, in particular caprylyl / capryl glucoside, as surfactant.

[0014] The state of the art is known in DE 69531870 T2, which discloses the use of sophorolipids in cosmetic products.

[0015] Sophorolipids are special glycolipids. They can be produced by fermentation of yeasts of the Candida and Torulopsis types, as well as Torulopsis magnoliae, Candida bombicola, Candida apicola, or Candida bogoriensis.

[0016] The essential glucid of extracellular sophorolipids is sophorose (2'-O-β-D-glucopyranosyl-β-D-glucopyranose). This sugar can be acetylated at the 6' and 6' positions and is linked to an i-ethyl hydroxyl group at the ω or ω-1 position. The lipid fraction of sophorolipids is composed of several hydroxy fatty acids.

[0017] Patent application EP0209783A describes sophorolipids and their use as an anti-dandruff agent and bacteriostatic agent.

[0018] The present invention provided a surprising solution to the problem.

[0019] The invention is a two-phase cosmetic or dermatological preparation comprising a horizontally separated two-phase system comprising an oil and an aqueous phase, characterized in that the preparation comprises a) sophorolipid and b) hyaluronic acid and / or their salts.

[0020] Surprisingly, the addition of at least one sophorolipid leads to significantly more transparent aqueous phases in the presence of hyaluronic acid and / or its salts. This is especially true after brief mixing of both phases by shaking and subsequent separation of the phases at rest.

[0021] Unless otherwise stated, all tests and measurements were performed under "normal conditions". The term "normal conditions" refers to 20°C, 1013 hPa, and 50% relative humidity.

[0022] The term "skin" refers exclusively to human skin.

[0023] Where weight percentages (wt%) are given below without reference to a specific composition or mixture, these percentages always refer to the total weight of the preparation. Where ratios of components / substances / groups of substances are disclosed below, these ratios refer to the weight ratios of the components / substances / groups of substances mentioned.

[0024] Where weight percentage ranges for the components of the preparation are specified below, the disclosure of the present application also includes all individual values ​​in steps of 0.1 wt.% within these weight percentage ranges.

[0025] The terms "according to the invention," "advantageous according to the invention," "advantageous within the meaning of the present invention," etc., always refer, within the scope of this disclosure, to the preparation according to the invention, the use according to the invention, and the process. The term "free from," within the meaning of this disclosure, means that the proportion of the substance in question does not exceed 0.1% by weight and, in particular, is 0% by weight, based on the total weight of the preparation. Thus, accidental introduction through impurities should not lead to exclusion from the scope of protection.

[0026] Emulsifiers are defined as all substances listed as "emulsifying agents" in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010 (ISBN 1-882621-47-6). Surfactants are defined as all substances listed as "surfactants" in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010 (ISBN 1-882621-47-6).

[0027] Where viscosity values ​​are given in this disclosure, all values ​​refer to a measurement at 25°C in a 150 ml wide-mouth bottle (VWR No.: 807-0001) using the Rheomat R 123 from proRheo GmbH. The Rheomat R 123 is a rotational viscometer, meaning that a measuring element rotates within the substance being measured. The force required to rotate the measuring element within the sample at a predetermined speed is measured. The viscosity is then calculated from this torque, the rotational speed of the measuring element, and the geometric dimensions of the measuring system. The measuring element used is No. 1 (article no. 200 0191), suitable for a viscosity range up to 10,000 mPa·s and a rotational speed of 62.5 min⁻¹.

[0028] When this disclosure refers to an average, that average always refers to arithmetic means.

[0029] If this disclosure mentions the molecular weight of polymers, this refers to a measurement of light scattering.

[0030] The term "transparent" here refers to a transmission measurement at 25°C at 880 nm. The higher the transmission, the more transparent the system.

[0031] Advantageously, the at least one sophorolipid is used in a proportion of 0.0001 to 3 wt.%, preferably 0.0005 to 1 wt.%, preferably 0.01 to 0.5 wt.% and particularly preferably 0.03 to 0.2 wt.%, based on the total mass of the aqueous phase of the preparation.

[0032] Furthermore, it is advantageous if hyaluronic acid and / or its salts are present in a proportion of 0.0001 to 0.5 wt.%, preferably 0.001 to 0.2 wt.%, preferably 0.005 to 0.1 wt.%, and particularly preferably 0.01 to 0.05 wt.%, where these values ​​refer to the total weight of the aqueous phase of the preparation. It is further advantageous if the weight ratio of hyaluronic acid and / or its salts to sophorolipid is 12:1 to 1:20, preferably 10:1 to 1:5, advantageously 7:1 to 1:1, and particularly preferably 6:1 to 2:1.

[0033] It is particularly advantageous to use the sodium salt of hyaluronic acid. Furthermore, it is advantageous if the average molecular weight of the hyaluronic acid is in the range of 1.8 to 10⁻⁶. 6 up to 2.5-10 6 That's where it lies.

[0034] Advantageously, the weight ratio of the aqueous phase to the oil phase contained in the preparation is from 98:2 to 50:50, preferably from 96:4 to 75:30, preferably from 94:6 to 85:15 and particularly preferably from 93:7 to 90:10.

[0035] The oil phase of the preparation according to the invention advantageously comprises one or more oils selected from the group consisting of isododecane, isohexadecane, isopropyl palmitate, undecane, C15-19 alkanes, and coco-caprylate / caprate.

[0036] It is advantageous if isododecane is included. If the oil phase comprises isododecane, it is advantageous if the total proportion of isododecane is 50.0 to 95 wt.%, preferably 60.0 to 93.0 wt.%, more preferably 75.0 to 90.0 wt.%, and particularly preferably 80.0 to 88.0 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0037] It is advantageous if isohexadecane is included. If the oil phase comprises isohexadecane, it is advantageous if the total proportion of isohexadecane is 2.0 to 60 wt.%, preferably 3.0 to 45 wt.%, preferably 4.0 to 35 wt.%, preferably 5.0 to 25 wt.%, and particularly preferably 6.0 to 20 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0038] It is advantageous if isopropyl palmitate is included. If the oil phase comprises isopropyl palmitate, it is advantageous if the total proportion of isopropyl palmitate is 0.1 to 30 wt.%, preferably 0.2 to 25 wt.%, preferably 0.3 to 10.0 wt.%, preferably 0.4 to 8.0 wt.%, and particularly preferably 0.5 to 6.5 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0039] It is advantageous if undecane is included. If the oil phase comprises undecane, it is advantageous if the total undecane content is 0.1 to 30 wt.%, preferably 0.2 to 25 wt.%, more preferably 0.3 to 10.0 wt.%, more preferably 0.4 to 8.0 wt.%, and particularly preferably 0.5 to 6.5 wt.%, in each case based on the total weight of the oil phase of the preparation. It is advantageous if alkanes are included. If the oil phase comprises 015-19 alkanes, it is advantageous if the total proportion of 015-19 alkanes is from 0.1 to 40 wt. %, preferably from 1.5 to 30.5 wt. %, preferably from 5.0 to 25.0 wt. %, preferably from 8.0 to 20.0 wt. %, and particularly preferably from 12.0 to 16.5 wt. %, in each case based on the total weight of the oil phase of the preparation.

[0040] It is advantageous if coco-caprylate / caprate is included. If the oil phase comprises coco-caprylate / caprate, it is advantageous if the total proportion of coco-caprylate / caprate is 0.1 to 10 wt.%, preferably 0.3 to 6.5 wt.%, more preferably 0.4 to 5.5 wt.%, more preferably 0.5 to 4.0 wt.%, and particularly preferably 0.6 to 3.2 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0041] Furthermore, it is advantageous if the oil phase includes undecane, ethylhexyl cocoate, dicaprylyl ether and / or octyldodecanol.

[0042] If undecane, ethylhexyl cocoate, dicaprylyl ether and / or octyldodecanol are included, it is preferred that the total proportion of these components is 1.0 to 60 wt.%, preferably 1.2 to 50 wt.%, preferably 1.4 to 25 wt.%, preferably 1.7 to 18 wt.% and particularly preferably 2.0 to 12 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0043] If undecane, ethylhexyl cocoate, dicaprylyl ether and / or octyldodecanol are included, it is preferred that the proportion of any of these components is 0.1 to 10 wt.%, preferably 0.3 to 6.5 wt.%, preferably 0.4 to 3.5 wt.%, preferably 0.5 to 2.0 wt.% and particularly preferably 0.6 to 1.2 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0044] Furthermore, it is advantageous if the oil phase comprises Helianthus Annuus Seed Oil, Vitis Vinifera Seed Oil and / or Argania Spinosa Kernel Oil. If Helianthus Annuus Seed Oil, Vitis Vinifera Seed Oil and / or Argania Spinosa Kernel Oil are included, it is preferred if the proportion of any one of these components is 0.1 to 10 wt.%, preferably 0.3 to 6.5 wt.%, preferably 0.4 to 3.5 wt.%, preferably 0.5 to 2.0 wt.%, and particularly preferably 0.6 to 1.2 wt.%, in each case based on the total weight of the oil phase of the preparation.

[0045] Furthermore, it is advantageous if the oil phase comprises one or more dyes. Advantageously selected dyes included in the oil phase are from the group consisting of CI 61565, CI 60725, Haematococcus Pluvialis, and CI 75130. Preferred embodiments of the invention are further advantageously characterized in that they are free of silicone oils and / or silicone components. By definition, silicone components are understood to be liquid substances under normal conditions that contain an alkyl silicon group. "Free of" in this context means that these components are not present.

[0046] Furthermore, it is advantageous if sodium chloride is included in the cosmetic preparation. If sodium chloride is included, it is preferred if the proportion of sodium chloride is 0.01 to 2.0 wt.%, preferably 0.1 to 1.1 wt.%, and particularly preferably 0.4 to 0.8 wt.%, based on the aqueous phase of the cosmetic preparation.

[0047] Other advantageous formulations are advantageously free of sodium chloride.

[0048] Advantageous embodiments of the invention are further characterized in that the preparation contains additional surfactants in proportions of less than 0.6 wt.%, preferably less than 0.4 wt.%, preferably less than 0.3 wt.%, preferably less than 0.2 wt.%, preferably less than 0.1 wt.%, and particularly preferably in a proportion of 0 wt.%, based on the total weight of the aqueous phase of the preparation. Consequently, it is particularly preferred that no additional surfactants are contained.

[0049] According to the invention, it is advantageous if the preparation is free of benzethonium chloride. Accordingly, the preparation advantageously contains no benzethonium chloride.

[0050] Furthermore, it is advantageous within the meaning of the present invention if the preparation is characterized in that it comprises trisodium EDTA. If trisodium EDTA is included, it is advantageous if the total proportion of trisodium EDTA is between 0.01 and 0.4% by weight, based on the total weight of the preparation.

[0051] Furthermore, it is advantageous within the meaning of the present invention if the preparation is characterized in that it comprises EDDS (ethylenediamine succinic acid) or its salts. If EDDS and / or its salts are included, it is advantageous if the total proportion of EDDS and / or its salts is between 0.01 and 0.4% by weight, based on the total weight of the preparation.

[0052] Furthermore, it is advantageous according to the present invention if the preparation is characterized in that it comprises glycerin. If glycerin is included, it is advantageous if it is present in a proportion of 0.1 to 5 wt.%, preferably 1.0 to 4.5 wt.%, and particularly preferably 1.5 to 4.0 wt.%, based on the total weight. Furthermore, it is advantageous according to the present invention if the preparation is characterized in that it comprises phenoxyethanol. If phenoxyethanol is included, it is advantageous if it is present in a proportion of 0.1 to 1.0 wt.%, preferably 0.15 to 0.8 wt.%, and particularly preferably 0.2 to 0.6 wt.%, based on the total weight.

[0053] Furthermore, it is advantageous if the water phase comprises water. If water is included, it is further advantageous if the total water content, based on the total weight of the water phase, is more than 90 wt.%, preferably more than 92 wt.%, preferably more than 94 wt.%, preferably more than 96 wt.%, and less than 98 wt.%.

[0054] Furthermore, it is advantageous if the aqueous phase of the preparation includes one or more water-soluble dyes, in particular CI 16035 (FD&C Red 40; 6-Hydroxy-5-((6- methoxy-4-sulfo-m-tolyl)azo)-2-naphthalenesuifonic acid disodium salt).

[0055] Another noteworthy factor with two-phase products is their filling ratio. Finding the right balance between the water and oil phases proved crucial for optimal cleaning performance. Too little oil negatively impacts cleaning efficiency.

[0056] Since two-phase preparations are frequently used as cleansing agents and especially as eye makeup removers, very good tolerability is particularly important in the area around the eye. This is achieved by the preparation according to the invention.

[0057] Advantageously, the preparations according to the invention comprise less than 0.01 wt.%, in particular 0 wt.%, of polymers and / or thickeners, in each case based on the total mass of the preparation.

[0058] The preparations of the invention may further comprise cosmetic ingredients such as are commonly used in such formulations. These include additional colorants, perfume ingredients, or skin-conditioning agents.

[0059] Examples

[0060] The following example formulations are intended to illustrate the present invention. Numerical values ​​refer to weight percentages based on the total mass of the preparation. The following table shows the composition of the aqueous and oil phases of the example formulations. The mixing ratio of the aqueous and oil phases, expressed as weight percent, is also given in the first column. All values ​​are expressed as weight percent.

[0061] The oil and water phases were prepared separately, analogous to the description above. 20 mL of the water phase were taken before mixing with the oil phase and placed in a 30 mL Turbiscan vial. The transmission of the water phase was measured in standard 30 mL cylindrical vials at a height of 30 mm from the bottom of the vial at a wavelength of 880 nm and 25 °C using MICROTRAC TURBISCAN AGS. The higher transmission value indicates that the water phase is clearer. It is crucial for the production process that the water phase is as clear as possible. Otherwise, quality control cannot ensure that the water phase is not contaminated at the production center. The measured values ​​for the transmission of the pure water phase before mixing with the oil phase are given in the table above. In the table above, Example 4 represents an example according to the invention.All other examples are for comparison.

[0062] Subsequently, both phases were combined under normal conditions. The resulting products were mixed once and analyzed spectroscopically.

[0063] Specifically, 1.5 g of the oil phase and 18.5 g of the aqueous phase were placed in a 30 mL Turbiscan vial. The vial containing the two-phase formula was shaken vigorously by hand 20 times to ensure complete mixing of the phases. The transmission of the aqueous phase (at a height of 30 mm above the bottom of the vial) and the transmission of the oil phase (at a height of 37 mm above the bottom of the vial) were then measured hourly for 24 hours. The measurements were performed at 880 nm and 25°C using the MICROTRAC TURBISCAN AGS.

[0064] The specific transmission values ​​are given in the following table:

[0065] It is evident that, without benzethonium chloride, a comparable transparent formulation with respect to the oil and water phases in the presence of hyaluronic acid and / or its salts can only be achieved by the present invention.

[0066] Further example recipes;

Claims

Claims Claims 1. A two-phase cosmetic or dermatological preparation comprising a horizontally separated two-phase system comprising an oil and an aqueous phase, characterized in that the preparation comprises a) sophorolipid and b) hyaluronic acid and / or its salts, 2. Preparation according to claim 1 characterized in that the sophorolipid is contained in a proportion of 0.0001 to 3 wt.%, preferably 0.0005 to 1 wt.%, preferably 0.01 to 0.5 wt.% and particularly preferably 0.03 to 0.2 wt.%, based on the total mass of the aqueous phase of the preparation.

3. Preparation according to one of the preceding claims characterized in that hyaluronic acid and / or its salts are contained in a proportion of 0.0001 to 0.5 wt.%, preferably 0.001 to 0.2 wt.%, preferably 0.005 to 0.1 wt.% and particularly preferably 0.01 to 0.05 wt.%, wherein the values ​​refer to the total weight of the aqueous phase of the preparation.

4. Preparation according to one of the preceding claims characterized in that the weight ratio of hyaluronic acid and / or its salts to sophorolipid is from 12:1 to 1:20, preferably from 10:1 to 1:5, advantageously from 7:1 to 1:1 and particularly preferably from 6:1 to 2:

1.

5. Preparation according to one of the preceding claims characterized in that the hyaluronic acid is used as a sodium salt.

6. Preparation according to one of the preceding claims characterized in that the weight ratio of the aqueous phase to the oil phase contained in the preparation is from 98:2 to 50:50, preferably from 96:4 to 75:30, preferably from 94:6 to 85:15 and particularly preferably from 93:7 to 90:

10.

7. Preparation according to one of the preceding claims characterized in that the oil phase comprises one or more oils selected from the group consisting of isododecane, isohexadecane, isopropyl palmitate, undecane, C15-19 alkanes, and coco-caprylate / caprate.

8. Preparation according to one of the preceding claims characterized in that the oil phase comprises isododecane and the total proportion of isododecane is 50.0 to 95 wt.%, preferably 60.0 to 93.0 wt.%, preferably 75.0 to 90.0 wt.% and in particular preferably 80.0 to 88.0 wt.%, in each case based on the total weight of the oil phase of the preparation.

9. Preparation according to one of the preceding claims characterized in that the oil phase comprises isohexadecane and the total proportion of isohexadecane is 2.0 to 60 wt.%, preferably 3.0 to 45 wt.%, preferably 4.0 to 35 wt.%, preferably 5.0 to 25 wt.% and particularly preferably 6.0 to 20 wt.%, in each case based on the total weight of the oil phase of the preparation.

10. Preparation according to one of the preceding claims characterized in that the oil phase comprises one or more colorants.

11. Preparation according to one of the preceding claims characterized in that the preparation is free of silicone oils and / or silicone components.

12. Preparation according to one of the preceding claims characterized in that it contains sodium chloride and the proportion of sodium chloride is from 0.01 to 2.0 wt.%, preferably from 0.1 to 1.1 wt.% and particularly preferably from 0.4 to 0.8 wt.%, based on the aqueous phase of the cosmetic preparation.

13. Preparation according to one of claims 1 to 11 characterized in that it does not contain sodium chloride.

14. Preparation according to one of the preceding claims characterized in that the total water content, based on the total weight of the aqueous phase, is more than 90 wt.%, preferably more than 92 wt.%, preferably more than 94 wt.%, preferably more than 96 wt.%, and less than 98 wt.%.

15. Preparation according to one of the preceding claims characterized in that the aqueous phase of the preparation comprises one or more water-soluble dyes, in particular CI 16035 (FD&C Red 40; 6-Hydroxy-5-((6-methoxy-4-sulfo- m-tolyl)azo)-2-naphthalenesulfonic acid disodium salt).

Citation Information

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